Orthotrifluoromethyl containing phenylazonaphthol dyestuffs

ABSTRACT

Azo dyestuffs of the formula ##STR1## wherein R 1  denotes acyl, 
     R 2  denotes hydrogen, fluorine, chlorine or trifluoromethyl, 
     R 3  denotes hydrogen, optionally substituted C 1  -C 4  -alkyl, cyclohexyl or optionally substituted phenyl and 
     R 4  denotes hydrogen or C 1  -C 4  -alkyl group 
     are suitable for dyeing natural and synthetic fibre materials, for example for dyeing wool or polyamide fibres, in level read to violet shades with very good fastnesses to light, wet processing and perspiration, the color yield being good.

This is a continuation of co-pending application Ser. No. 391,090 filed June 22, 1982, abandoned, which in turn is a continuation of Ser. No. 884,960 filed Mar. 9, 1978, now abandoned.

The invention relates to azo dyestuffs which correspond, in the form of the free acid, to the formula ##STR2## wherein R₁ denotes acyl,

R₂ denotes hydrogen, fluorine, chlorine or trifluoromethyl,

R₃ denotes hydrogen, optionally substituted C₁ -C₄ -alkyl, cyclohexyl or optionally substituted phenyl and

R₄ denotes hydrogen or C₁ -C₄ -alkyl.

Preferably, the acylamino group is in the p-position relative to the azo group or in the p-position relative to the CF₃ group and the sulphonic acid group is in the m-position or p-position relative to the hydroxyl group.

Suitable acyl R₁ is, in particular, formyl, C₁ -C₈ -alkylcarbonyl which is optionally monosubstituted by chlorine, bromine, C₁ -C₄ -alkoxy, phenyl or methylphenyl, C₂ -C₄ -alkenylcarbonyl which is optionally monosubstituted by bromine, C₁ -C₄ -alkoxycarbonyl, phenoxycarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl which is optionally substituted by C₁ -C₄ -alkyl, aminocarbonyl which is optionally monosubstituted or disubstituted by C₁ -C₄ -alkyl or optionally monosubstituted by cyclohexyl, C₁ -C₄ -alkylcyclohexyl, phenyl, C₁ -C₄ -alkylphenyl, chlorophenyl, bromophenyl or trifluoromethylphenyl, benzoyl which is optionally substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, hydroxyl, C₁ -C₄ -alkylcarbonyloxy, chlorine, bromine, nitro or trifluoromethyl, naphthylcarbonyl, thenoyl, furoyl, pyridoyl, triazinyl which is substituted by fluorine, chlorine, OCH₃ or phenylamino, it being possible for phenylamino to be further substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, chlorine or bromine, pyrimidyl which is substituted by fluorine, chlorine, methyl or methylsulphonyl, quinoxaline-6-carbonyl which is substituted by chlorine, quinoxaline-6-sulphonyl which is substituted by chlorine, C₁ -C₄ -alkylsulphonyl, benzenesulphonyl which is optionally substituted by fluorine, chlorine, bromine, trifluoromethyl, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, nitro or C₁ -C₄ -alkylcarbonylamino, naphthylsulphonyl, cyclohexylsulphonyl or C₁ -C₄ -dialkylaminosulphonyl.

Possible substituents of the alkyl radicals R₃ are, in particular, hydroxyl, cyano, formylamino, C₁ -C₄ -alkylcarbonylamino or benzoylamino which is optionally substituted by methyl, chlorine, bromine or trifluoromethyl. Possible substituents of the phenyl radicals R₃ are C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, chlorine, bromine and trifluoromethyl.

Particularly suitable dyestuffs correspond, in the form of the free acid, to the formula ##STR3## wherein R₁ has the meaning indicated above.

R₁ preferably represents C₁ -C₄ -alkylcarbonyl, benzoyl which is optionally substituted by chlorine or methyl, C₁ -C₄ -alkylaminocarbonyl or phenylaminocarbonyl which is optionally substituted by methyl or chlorine.

The dyestuffs of the formula (I) are prepared either by diazotising amines of the formula ##STR4## and coupling the diazotisation products with coupling components of the formula ##STR5## wherein R₁, R₂, R₃ and R₄ have the abovementioned meaning,

or by acylating aminoazo dyestuffs of the formula ##STR6## wherein R₂, R₃ and R₄ have the abovementioned meaning,

with the introduction of the radical R₁.

Suitable acylating agents are, for example, carboxylic acid halides, carboxylic acid anhydrides, carbamic acid halides, sulphonic acid halides, sulphamic acid halides, isocyanates and heterocyclic compounds with anionic leaving groups.

The dyestuffs according to the invention are suitable for dyeing natural and synthetic fibre materials, for example for dyeing wool or polyamide fibres, in level red to violet shades with very good fastnesses to light, wet processing and perspiration, the colour yield being good. Depending on the substituents R₁, R₃ or R₄, they can be particularly suitable for dyeing polyamide fibres. For example, it is possible to prepare dyestuffs which are already taken up well on polyamide fibres from a neutral to weakly acid dyebath, and also those which are quantitatively taken up only from a weakly to more strongly acid dyebath. In the same manner, it is possible to advantageously influence the ease of combination with yellow and blue acid dyestuffs. Polyamide fibres are understood, in particular, as those consisting of synthetic polyamides, such as ε-polycaprolactam or condensation products of adipic acid and hexamethylenediamine.

Furthermore, dyestuffs of the formula (I) which carry a reactive acyl group are suitable for use as reactive dyestuffs, in accordance with the dyeing processes customary for these, for example for wool or cotton.

EXAMPLE 1

21.8 g of 3-acetylamino-6-amino-benzotrifluoride are dissolved in 350 ml of water and 30 ml of concentrated hydrochloric acid and the solution is cooled to 0° C. and diazotised with a solution of 6.9 g of sodium nitrite in 50 ml of water. After destroying excess nitrous acid with amidosulphonic acid, the diazonium salt solution is added to a solution, cooled to 5° C., of 24.2 g of 6-amino-4-hydroxynaphthalene-2-sulphonic acid in 300 ml of dimethylformamide, which has previously been adjusted to pH 1 by adding about 5 ml of concentrated hydrochloric acid. The coupling is completed very rapidly at this pH value. The mixture is subsequently stirred for 2 hours at room temperature. The reaction product is then filtered off and dried. This gives 44 g of a red powder of the formula ##STR7## which dyes polyamide fibres in a clear bluish-tinged red from an aqueous solution. A clear, somewhat bluish-tinged red is obtained with this dyestuff on wool.

The 3-acetylamino-6-amino-benzotrifluoride used as the diazo component was obtained as follows:

2-Amino-5-nitrobenzotrifluoride (melting point 91°-92° C.) is catalytically reduced in methanol (Raney nickel as the catalyst). The 2,5-diaminobenzotrifluoride (melting point: 54° to 55° C.) thus obtainable is converted into 3-acetylamino-6-benzotrifluoride (melting point 125° to 126° C.) with acetic anhydride in glacial acetic acid, with the addition of sodium acetate.

EXAMPLE 2

45.6 g of the dyestuff of the formula ##STR8## obtained by coupling diazotised 2-amino-5-nitrobenzotrifluoride with 6-amino-4-hydroxynaphthalene-2-sulphonic acid, are dissolved in 400 ml of water by adding an amount of 20% strength sodium hydroxide solution such that the pH value is 7 to 8. After warming the solution to 30° C., 36 g of Na₂ S.9H₂ O, dissolved in 100 ml of water, are added dropwise in the course of 1 hour. The mixture is then subsequently stirred for 1 hour at room temperature. The pH is adjusted to 7 by adding a little hydrochloric acid. Benzoyl chloride and 20% strength sodium hydroxide solution are then added dropwise simultaneously from two dropping funnels. The temperature is kept at 15° to 20° C. by external cooling and the pH value is kept at 5 to 7. After adding 18 g of benzoyl chloride, the acylation has ended, which can be easily determined by following the reaction with a thin layer chromatogram. The dye-stuff is completely precipitated by adding 80 g of sodium chloride and is filtered off.

It has the formula ##STR9##

After drying, 49 g of a dark red powder are obtained which dyes polyamide fibres in a bluish-tinged red shade from an aqueous solution.

This dyestuff is also obtained by diazotising 3-benzoyl-amino-6-aminobenzotrifluoride (melting point: 128° to 129° C.) and coupling the diazonium salt with 6-amino-4-hydroxynaphthalene-2-sulphonic acid.

EXAMPLE 3

0.1 g of the dyestuff obtained according to Example 1 is dissolved hot in 100 ml of water. 5 ml of ammonium acetate solution are added and the mixture is diluted to a volume of 500 ml with cold water. 10 g of polyamide fibre material are put into this dyebath and the dyebath is heated to the boil in the course of 20 minutes, 4 ml of 10% strength acetic acid are added and the mixture is kept at the boiling point for 1 hour. Thereafter, the dyed polyamide is taken out of the dyebath, rinsed thoroughly with hot water and dried at 70° to 80° C. This gives a clear bluish-tinged red dyeing.

According to the process indicated in Example 1, when the diazo components and coupling components listed in the table which follows are used, further valuable water-soluble dyestuffs which dye polyamide in the shades indicated from a weakly acid or neutral bath are obtained. The same dyestuffs are also each obtainable, according to the process of Example 2, from the dyestuffs of the formula (V) ##STR10## and a corresponding acylating component.

                  TABLE 1                                                          ______________________________________                                         Ex-                                                                            am-                                 Colour                                     ple  Diazo component                                                                               Coupling component                                                                             shade                                      ______________________________________                                         4    2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-formylamino- naphthalene-6-  bluish-                                         aniline        sulphonic acid  tinged                                                                         red                                        5    2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-propionylamino-                                                                             naphthalene-6-  bluish-                                         aniline        sulphonic acid  tinged                                                                         red                                        6    2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-butyrylamino-                                                                               naphthalene-6-  bluish-                                         aniline        sulphonic acid  tinged                                                                         red                                        7    2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy                                                                              strongly                                        4-butylcarbonyl-                                                                              naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        8    2-Trifluoromethyl                                                                             2-Amino-8-hydroxy-                                                                             strongly                                        4-amylcarbonyl-                                                                               naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        9    2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-isobutylcar- naphthalene-6-  bluish-                                         bonylaminoaniline                                                                             sulphonic acid  tinged                                                                         red                                        10   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-sec.-butylcar-                                                                              naphthalene-6-  bluish-                                         bonylaminoaniline                                                                             sulphonic acid  tinged                                                                         red                                        11   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy                                                                              strongly                                        4-tert.-butylcar-                                                                             naphthalene-6-  bluish-                                         bonylaminoaniline                                                                             sulphonic acid  tinged                                                                         red                                        12   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(1-ethylpropyl)-                                                                            naphthalene-6-  bluish-                                         carbonylamino- sulphonic acid  tinged                                          aniline                        red                                        13   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(1-ethylamyl)-                                                                              naphthalene-6-  bluish-                                         carbonylamino- sulphonic acid  tinged                                          aniline                        red                                        14   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy                                                                              bluish-                                         4-chloroacetyl-                                                                               naphthalene-6-  tinged                                          aminoaniline   sulphonic acid  red                                        15   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-(2-chloroethyl)-                                                                            naphthalene-6-  tinged                                          carbonylamino- sulphonic acid  red                                             aniline                                                                   16   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-(3-chloropropyl)-                                                                           naphthalene-6-  tinged                                          carbonylamino- sulphonic acid  red                                             aniline                                                                   17   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-acryloylamino-                                                                              naphthalene-6-  bluish-                                         aniline        sulphonic acid  tinged                                                                         red                                        18   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-methacryloyl-                                                                               naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        19   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-bromoacryloyl-                                                                              naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        20   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(1,2-dibromo-                                                                               naphthalene-6-  bluish-                                         ethyl)-carbonyl-                                                                              sulphonic acid  tinged                                                                         red                                        21   2-Trifluoromethyl                                                                             2-Amino-8-hydroxy-                                                                             strongly                                        4-methoxyacetyl-                                                                              naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        22   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-methoxycarbonyl-                                                                            naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        23   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-ethoxycarbonyl-                                                                             naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        24   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-propoxycarbonyl-                                                                            naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        25   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-isopropoxycar-                                                                              naphthalene-6-  bluish-                                         bonylaminoaniline                                                                             sulphonic acid  tinged                                                                         red                                        26   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-butoxycarbonyl-                                                                             naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        27   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-phenoxycarbonyl-                                                                            naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        28   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-benzylcarbonyl-                                                                             naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        29   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(4-methylbenzyl)-                                                                           naphthalene-6-  bluish-                                         carbonylamino- sulphonic acid  tinged                                          aniline                        red                                        30   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(4-methoxy-  naphthalene-6-  bluish-                                         benzyl)-carbonyl-                                                                             sulphonic acid  tinged                                          aminoaniline                   red                                        31   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-phenoxyacetyl-                                                                              naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        32   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(4-chloro-   naphthalene-6-  bluish-                                         phenoxy)-acetyl-                                                                              sulphonic acid  tinged                                          aminoaniline                   red                                        33   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(3-methyl-   naphthalene-6-  bluish-                                         phenoxy)-acetyl-                                                                              sulphonic acid  tinged                                          aminoaniline                   red                                        34   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-dimethylamino-                                                                              naphthalene-6-  tinged                                          carbonylamino- sulphonic acid  red                                             aniline                                                                   35   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-diethylaminocar-                                                                            naphthalene-6-  tinged                                          bonylaminoaniline                                                                             sulphonic acid  red                                        36   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-methylaminocar-                                                                             naphthalene-6-  tinged                                          bonylaminoaniline                                                                             sulphonic acid  red                                        37   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-propylaminocar-                                                                             naphthalene-6-  tinged                                          bonylaminoaniline                                                                             sulphonic acid  red                                        38   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-butylaminocar-                                                                              naphthalene-6-  tinged                                          bonylaminoaniline                                                                             sulphonic acid  red                                        39   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-tert.-butyl- naphthalene-6-  tinged                                          aminocarbonyl- sulphonic acid  red                                             aminoaniline                                                              40   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-cyclopentylamino-                                                                           naphthalene-6-  tinged                                          carbonylamino- sulphonic acid  red                                             aniline                                                                   41   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-cyclohexylamino-                                                                            naphthalene-6-  tinged                                          carbonylamino- sulphonic acid  red                                             aniline                                                                   42   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-cylcohexylcar-                                                                              naphthalene-6-  tinged                                          bonylaminoaniline                                                                             sulphonic acid  red                                        43   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-(4-methylcyclo-                                                                             naphthalene-6-  tinged                                          hexyl)-carbonyl-                                                                              sulphonic acid  red                                             aminoaniline                                                              44   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         4-(2-methylcyclo-                                                                             naphthalene-6-  tinged                                          hexyl)-carbonyl-                                                                              sulphonic acid  red                                             aminoaniline                                                              45   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(4-methylbenzoyl)-                                                                          naphthalene-6-                                                  aminoaniline   sulphonic acid                                             46   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(2-methylbenzoyl-                                                                           naphthalene-6-                                                  aminoaniline   sulphonic acid                                             47   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(4-methoxybenz-                                                                             naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             48   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(2-methoxybenz-                                                                             naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             49   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(3-methoxybenz-                                                                             naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             50   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(2-ethoxybenz-                                                                              naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             51   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy                                                                              claret                                          4-(2-butoxybenz-                                                                              naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             52   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(2-hydroxybenz-                                                                             naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             53   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(2-acetoxybenz-                                                                             naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             54   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy                                                                              claret                                          4-(4-chlorobenz-                                                                              naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             55   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(3-chlorobenz-                                                                              naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             56   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(2-chlorobenz-                                                                              naphthalene-6-                                                  oyl)-aminoaniline                                                                             sulphonic acid                                             57   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(4-bromobenzoyl)-                                                                           naphthalene-6-                                                  aminoaniline   sulphonic acid                                             58   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(4-fluorobenzoyl)-                                                                          naphthalene-6-                                                  aminoaniline   sulphonic acid                                             59   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(3-nitrobenzoyl)-                                                                           naphthalene-6-                                                  aminoaniline   sulphonic acid                                             60   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-(3-trifluoro-                                                                               naphthalene-6-                                                  methylbenzoyl)-                                                                               sulphonic acid                                                  aminoaniline                                                              61   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-phenylaminocar-                                                                             naphthalene-6-  bluish-                                         bonylaminoaniline                                                                             sulphonic acid  tinged                                                                         red                                        62   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-acetylamino- naphthalene-5-  bluish-                                         aniline        sulphonic acid  tinged                                                                         red                                        63   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-butylcarbonyl-                                                                              naphthalene-5-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        64   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(1-ethylpentyl)-                                                                            naphthalene-5-  bluish-                                         carbonylamino- sulphonic acid  tinged                                          aniline                        red                                        65   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(3-chloropropyl)-                                                                           naphthalene-5-  bluish-                                         carbonylamino- sulphonic acid  tinged                                          aniline                        red                                        66   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-acryloylamino-                                                                              naphthalene-5-  bluish-                                         aniline        sulphonic acid  tinged                                                                         red                                        67   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(1,2-dibromo-                                                                               naphthalene-5-  bluish-                                         propionylamino-                                                                               sulphonic acid  tinged                                          aniline                        red                                        68   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-methoxycarbonyl-                                                                            naphthalene-5-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        69   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-benzylcarbonyl-                                                                             naphthalene-5-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        70   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(2,4-dichloro-                                                                              naphthalene-5-  bluish-                                         phenoxy)-acetyl-                                                                              sulphonic acid  tinged                                          aminoaniline                   red                                        71   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-diethylamino-                                                                               naphthalene-5-  bluish-                                         carbonylamino- sulphonic acid  tinged                                          aniline                        red                                        72   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-cyclohexylcar-                                                                              naphthalene-5-  bluish-                                         bonylaminoaniline                                                                             sulphonic acid  tinged                                                                         red                                        73   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-benzoylamino-                                                                               naphthalene-5-                                                  aniline        sulphonic acid                                             74   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-4-chlorobenzoyl)-                                                                           naphthalene-5-                                                  aminoaniline   sulphonic acid                                             75   2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-phenylaminocar-                                                                             naphthalene-5-                                                  bonylaminoaniline                                                              4-phenylaminocar-                                                                             naphthalene-5-                                                  bonylaminoaniline                                                                             sulphonic acid                                             76   2-Trifluoromethyl-                                                                            2-Methylamino-8-                                                                               red                                             4-acetylamino- hydroxynaphtha-                                                 aniline        lene-6-sulphonic                                                               acid                                                       77   2-Trifluoromethyl-                                                                            2-Methylamino-8-                                                                               bluish-                                         4-benzoylamino-                                                                               hydroxynaphtha- tinged                                          aniline        lene-6-sulphonic                                                                               red                                                            acid                                                       78   2-Trifluoromethyl-                                                                            2-Methylamino-8-                                                                               red                                             4-benzylcarbonyl-                                                                             hydroxynaphtha-                                                 aminoaniline   lene-6-sulphonic                                                               acid                                                       79   2-Trifluoromethyl-                                                                            2-Methylamino-8-                                                                               red                                             4-(4-chlorophenoxy)-                                                                          hydroxynaphtha-                                                 acetylaminoaniline                                                                            lene-6-sulphonic                                                               acid                                                       80   2-Trifluoromethyl-                                                                            2-Methylamino-8-                                                                               red                                             4-butylsulphonyl-                                                                             hydroxynaphtha-                                                 aminoaniline   lene-6-sulphonic                                                               acid                                                       81   2-Trifluoromethyl-                                                                            2-Methylamino-8-                                                                               bluish-                                         4-phenylsulphonyl-                                                                            hydroxynaphtha- tinged                                          aminoaniline   lene-6-sulphonic                                                                               red                                                            acid                                                       82   2-Trifluoromethyl-                                                                            2-Methylamino-8-                                                                               bluish-                                         4-dimethylaminocar-                                                                           hydroxynaphtha- tinged                                          bonylaminoaniline                                                                             lene-6-sulphonic                                                                               red                                                            acid                                                       83   2-Trifluoromethyl-                                                                            2-Dimethylamino-8-                                                                             red                                             4-acetylamino- hydroxynaphthalene-                                             aniline        6-sulphonic acid                                           84   2-Trifluoromethyl-                                                                            2-Dimethylamino-8-                                                                             bluish-                                         4-benzoylamino-                                                                               hydroxynaphtha- tinged                                          aniline        lene-6-sulphonic                                                                               red                                                            acid                                                       85   2-Trifluoromethyl-                                                                            2-Butylamino-8- red                                             4-acetylamino- hydroxynaphtha-                                                 aniline        lene-6-sulphonic                                                               acid                                                       86   2-Trifluoromethyl-                                                                            2-Butylamino-8- bluish-                                         4-benzoylamino-                                                                               hydroxynaphtha- tinged                                          aniline        lene-6-sulphonic                                                                               red                                                            acid                                                       87   2-Trifluoromethyl-                                                                            2-(2-Hydroxyethyl-                                                                             red                                             4-acetylamino- amino)-8-hydroxy-                                               aniline        naphthalene-6-                                                                 sulphonic acid                                             88   2-Trifluoromethyl-                                                                            2-(2-Hydroxyethyl-                                                                             red                                             4-(1-ethylpentyl)-                                                                            amino)-8-hydroxy-                                               carbonylamino- naphthalene-6-                                                  aniline        sulphonic acid                                             89   2-Trifluoromethyl-                                                                            2-(2-Hydroxyethyl-                                                                             bluish-                                         4-benzoylamino-                                                                               amino)-8-hydroxy                                                                               tinged                                          aniline        naphthalene-6-  red                                                            sulphonic acid                                             90   2-Trifluoromethyl-                                                                            2-(2-Cyanoethyl-                                                                               red                                             4-acetylamino- amino)-8-hydroxy-                                               aniline        naphthalene-6-                                                                 sulphonic acid                                             91   2-Trifluoromethyl-                                                                            2-(2-Cyanoethyl-                                                                               bluish-                                         4-benzoylamino-                                                                               amino)-8-hydroxy-                                                                              tinged                                          aniline        naphthalene-6-  red                                                            sulphonic acid                                             92   2-Trifluoromethyl-                                                                            2-(2-Acetylamino-                                                                              red                                             4-acetylamino  ethylamino)-8-                                                  aniline        hydroxynaphthalene-                                                            6-sulphonic acid                                           93   2-Trifluoromethyl-                                                                            2-(2-Acetylamino-                                                                              bluish-                                         4-benzoylamino-                                                                               ethylamino)-8-  tinged                                          aniline        hydroxynaphthalene-                                                                            red                                                            6-sulphonic acid                                           94   2-Trifluoromethyl-                                                                            2-(2-Benzoylamino-                                                                             red                                             4-acetylamino- ethylamino)-8-                                                  aniline        hydroxynaphthalene-                                                            6-sulphonic acid                                           95   2-Trifluoromethyl-                                                                            2-Cyclohexylamino-8-                                                                           red                                             4-acetylamino- hydroxynaphthalene-                                             aniline        6-sulphonic acid                                           96   2-Trifluoromethyl-                                                                            2-Cyclohexylamino-8-                                                                           bluish-                                         4-benzolyamino-                                                                               hydroxynaphthalene-                                                                            tinged                                          aniline        6-sulphonic acid                                                                               red                                        97   2-Trifluoromethyl-                                                                            2-Anilino-8-hydroxy-                                                                           strongly                                        4-acetylamino- naphthalene-6-  bluish-                                         aniline        sulphonic acid  tinged                                                                         red                                        98   2-Trifluoromethyl-                                                                            2-Dimethylamino-8-                                                                             red                                             4-acetylamino- hydroxynaphthalene-                                             aniline        5-sulphonic acid                                           99   2-Trifluoromethyl-                                                                            2-Anilino-8-hydroxy-                                                                           bluish-                                         4-acetylamino- naphthalene-5-  tinged                                          aniline        sulphonic acid  red                                        100  2-Trifluoromethyl-                                                                            2-Anilino-8-hydroxy-                                                                           bluish-                                         4-benzoylamino-                                                                               naphthalene-5-  tinged                                          aniline        sulphonic acid  red                                        101  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-formylamino-5-                                                                              naphthalene-6-  bluish-                                         chloroaniline  sulphonic acid  tinged                                                                         red                                        102  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-acetylamino-5-                                                                              naphthalene-6-  bluish-                                         chloroaniline  sulphonic acid  tinged                                                                         red                                        103  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-(1-ethylpentyl)-                                                                            naphthalene-6-  bluish-                                         carbonylamino-5-                                                                              sulphonic acid  tinged                                          chloroaniline                  red                                        104  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-acryloylamino-5-                                                                            naphthalene-6-  bluish-                                         chloroaniline  sulphonic acid  tinged                                                                         red                                        105  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy                                                                              strongly                                        4-(1,2-dibromopro-                                                                            naphthalene-6-  bluish-                                         pionyl)-amino-5-                                                                              tinged                                                          chloroaniline                  red                                        106  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             claret                                          4-benzoylamino-5-                                                                             naphthalene-6-                                                  chloroaniline  sulphonic acid                                             107  2,5-Bis-trifluoro-                                                                            2-Amino-8-hydroxy                                                                              violet                                          methyl-4-acetyl-                                                                              naphthalene-6-                                                  aminoaniline   sulphonic acid                                             108  2,5-Bis-trifluoro-                                                                            2-Amino-8-hydroxy                                                                              violet                                          methyl-4-methyl-                                                                              naphthalene-6-                                                  sulphonylamino-                                                                               sulphonic acid                                                  aniline                                                                   109  2,5-Bis-trifluoro-                                                                            2-Amino-8-hydroxy-                                                                             violet                                          methyl-4-benzoyl-                                                                             naphthalene-6-                                                  aminoaniline   sulphonic acid                                             110  2,5-Bis-trifluoro-                                                                            2-Amino-8-hydroxy-                                                                             violet                                          methyl-4-phenyl-                                                                              naphthalene-6-                                                  sulphonylamino-                                                                               sulphonic acid                                                  aniline                                                                   111  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-acetylamino-5-                                                                              naphthalene-5-  bluish-                                         chloroaniline  sulphonic acid  tinged                                                                         red                                        112  2,5-Bis-trifluoro-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        methyl-4-acetyl-                                                                              naphthalene-5-  bluish-                                         aminoaniline                   tinged                                                                         red                                        113  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-acetylamino- naphthalene-6-  tinged                                          aniline        sulphonic acid  red                                        114  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-(2-chloroethyl)-                                                                            naphthalene-6-  tinged                                          carbonylamino- sulphonic acid  red                                             aniline                                                                   115  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-(1-ethylpropyl)-                                                                            naphthalene-6-  tinged                                          carbonylamino- sulphonic acid  red                                             aniline                                                                   116  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-(1-ethylpentyl-                                                                             naphthalene-6-  tinged                                          carbonylamino- sulphonic acid  red                                             aniline                                                                   117  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-methacryloyl-                                                                               naphthalene-6-  tinged                                          aminoaniline   sulphonic acid  red                                        118  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy                                                                              bluish-                                         5-(1,2-dibromo-                                                                               naphthalene-6-  tinged                                          ethyl)-carbonyl-                                                                              sulphonic acid  red                                             aminoaniline                                                              119  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy                                                                              bluish-                                         5-methoxycarbonyl-                                                                            naphthalene-6-  tinged                                          aminoaniline   sulphonic acid  red                                        120  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-benzylcarbonyl-                                                                             naphthalene-6-  tinged                                          aminoaniline   sulphonic acid  red                                        121  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-phenoxyacetyl-                                                                              naphthalene-6-  tinged                                          aminoaniline   sulphonic acid  red                                        122  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish                                          5-dimethylamino-                                                                              naphthalene-6-  tinged                                          carbonylamino- sulphonic acid  red                                             aniline                                                                   123  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        5-benzoylamino-                                                                               naphthalene-6-  bluish-                                         aniline        sulphonic acid  tinged                                                                         red                                        124  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        5-(4-chlorobenz-                                                                              naphthalene-6-  bluish-                                         oyl)-aminoaniline                                                                             sulphonic acid  tinged                                                                         red                                        125  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        5-(3-trifluoro-                                                                               naphthalene-6-  bluish-                                         methylbenzoyl)-                                                                               sulphonic acid  tinged                                          aminoaniline                   red                                        126  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-(2-chloroethyl)-                                                                            naphthalene-6-  tinged                                          sulphonylamino-                                                                               sulphonic acid  red                                             aniline                                                                   127  2-trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-butylsulphonyl-                                                                             naphthalene-6-  tinged                                          aminoaniline   sulphonic acid  red                                        128  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-phenylsulphonyl-                                                                            naphthalene-6-  tinged                                          aminoaniline   sulphonic acid  red                                        129  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-dimethylamino-                                                                              naphthalene-6-  tinged                                          sulphonylamino-                                                                               sulphonic acid  red                                             aniline                                                                   130  2-Trifluoromethyl-                                                                            2-Methylamino-8-                                                                               bluish-                                         5-acetylamino- hydroxynaphthalene-                                                                            tinged                                          aniline        6-sulphonic acid                                                                               red                                        131  2-Trifluoromethyl-                                                                            2-Dimethylamino-8-                                                                             bluish-                                         5-acetylamino- hydroxynaphthalene-                                                                            tinged                                          aniline        6-sulphonic acid                                                                               red                                        132  2-Trifluoromethyl-                                                                            2-(2-Cyanoethylamino)-                                                                         bluish-                                         5-acetylamino- 8-hydroxynaphthalene-                                                                          tinged                                          aniline        6-sulphonic acid                                                                               red                                        .33  2-Trifluoromethyl-                                                                            2-(2-Hydroxyethyl-                                                                             bluish-                                         5-acetylamino- amino)-8-hydroxy-                                                                              tinged                                          aniline        naphthalene-6-  red                                                            sulphonic acid                                             134  2-Trifluoromethyl-                                                                            2-Butylamino-8- bluish-                                         5-acetylamino- hydroxynaphthalene-                                                                            tinged                                          aniline        6-sulphonic acid                                                                               red                                        135  2-Trifluoromethyl-                                                                            2-Cyclohexylamino-8-                                                                           bluish-                                         5-acetylamino- hydroxynaphthalene-                                                                            tinged                                          aniline        6-sulphonic acid                                                                               red                                        136  2-Trifluoromethyl-                                                                            2-(2-Acetylaminoethyl-                                                                         bluish-                                         5-acetylamino- amino)-8-hydroxy-                                                                              tinged                                          aniline        naphthalene-6-sul-                                                                             red                                                            phonic acid                                                137  2-Trifluoromethyl-                                                                            2-Anilino-8-hydroxy-                                                                           strongly                                        5-acetylamino- naphthalene-6-  bluish-                                         aniline        sulphonic acid  tinged                                                                         red                                        138  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             bluish-                                         5-acetylamino- naphthalene-5-  tinged                                          aniline        sulphonic acid  red                                        139  2-Trifluoromethyl-                                                                            2-Methylamino-8-                                                                               bluish-                                         5-acetylamino- hydroxynaphthalene-                                                                            tinged                                          aniline        5-sulphonic acid                                                                               red                                        140  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-chloro-5-acetyl-                                                                            naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        141  2,4-Bis-trifluoro-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        methyl-5-acetyl-                                                                              naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        142  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-chloro-5-benz-                                                                              naphthalene-6-  bluish-                                         oylaminoaniline                                                                               sulphonic acid  tinged                                                                         red                                        143  2,4-Bis-trifluoro-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        methyl-5-benzoyl-                                                                             naphthalene-6-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        144  2-Trifluoromethyl-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        4-chloro-5-acetyl-                                                                            naphthalene-5-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        145  2,4-Bis-trifluoro-                                                                            2-Amino-8-hydroxy-                                                                             strongly                                        methyl-5-acetyl-                                                                              naphthalene-5-  bluish-                                         aminoaniline   sulphonic acid  tinged                                                                         red                                        ______________________________________                                    

In Table 2, further polyamide dyestuffs are given which have been obtained by acylating the dyestuff of the formula ##STR11## on the amino group of the benzene ring with the acylating agents given in the table.

                  TABLE 2                                                          ______________________________________                                                                        Colour                                          Example                                                                               Acylating agent         shade                                           ______________________________________                                         146    4-Methylphenyl isocyanate                                                                              strongly                                                                       bluish-                                                                        tinged red                                      147    2,4-Dimethylphenyl isocyanate                                                                          strongly                                                                       bluish-                                                                        tinged red                                      148    4-Chlorophenyl isocyanate                                                                              strongly                                                                       bluish-                                                                        tinged red                                      149    3-Trifluoromethylphenyl isocyanate                                                                     strongly                                                                       bluish-                                                                        tinged red                                      150    Naphthalene-1-carboxylic acid                                                                          claret                                                 chloride                                                                151    Thiophene-2-carboxylic acid chloride                                                                   claret                                          152    Furane-2-carboxylic acid chloride                                                                      claret                                          153    Pyridine-4-carboxylic acid chloride                                                                    claret                                          154    Pyridine-3-carboxylic acid chloride                                                                    claret                                          155    Methanesulphonic acid chloride                                                                         strongly                                                                       bluish-                                                                        tinged red                                      156    Chloromethanesulphonic acid chloride                                                                   strongly                                                                       bluish-                                                                        tinged red                                      157    2-Chloroethanesulphonic acid                                                                           strongly                                               chloride                bluish-                                                                        tinged red                                      158    Butanesulphonic acid chloride                                                                          strongly                                                                       bluish-                                                                        tinged red                                      159    Benzenesulphonyl chloride                                                                              claret                                          160    4-Toluenesulphonyl chloride                                                                            claret                                          161    2-Toluenesulphonyl chloride                                                                            claret                                          162    4-Chlorobenzenesulphonyl chloride                                                                      claret                                          163    2,4-Dichlorobenzenesulphonyl chloride                                                                  claret                                          164    4-Methoxybenzenesulphonyl chloride                                                                     claret                                          165    3-Trifluoromethylbenzenesulphonyl                                                                      claret                                                 chloride                                                                166    4-Acetylaminobenzenesulphonyl chloride                                                                 claret                                          167    3-Nitrobenzenesulphonyl chloride                                                                       claret                                          168    Naphthalene-1-sulphonyl chloride                                                                       claret                                          169    Naphthalene-2-sulphonyl chloride                                                                       claret                                          170    Cyclohexanesulphonyl chloride                                                                          bluish-                                                                        tinged red                                      171    Dimethylsulphamic acid chloride                                                                        bluish-                                                                        tinged red                                      ______________________________________                                    

Further polyamide dyestuffs are obtained by acylating the dyestuff of the formula ##STR12## in the benzene amino group with the acylating agents given in Table 3 which follows.

                  TABLE 3                                                          ______________________________________                                         Example Acylating agent    Colour shade                                        ______________________________________                                         172     Butyl isocyanate   strongly bluish-                                                               tinged red                                          173     Naphthalene-1-carboxylic acid                                                                     violet                                                      chloride                                                               174     Ethanesulphonyl chloride                                                                          bluish-tinged red                                   175     Benzenesulphonyl chloride                                                                         violet                                              ______________________________________                                    

EXAMPLE 176

42.6 g of the dyestuff of the formula ##STR13## (prepared by reducing the corresponding nitro compound according to Example 2 and isolating the product at pH=7) are dissolved in 300 ml of water and 300 ml of acetone and the solution is cooled to 5° C. 30 g of 5-chloro-2,4,6-trifluoropyrimidine are then added dropwise in the course of 1 hour, whilst stirring well. The pH value is kept at 7 by simultaneously adding 10% strength sodium carbonate solution dropwise. When the amino group in the para-position relative to the azo group has been quantitatively acylated, which can be easily followed by thin layer chromatography, 50 g of sodium chloride are also added and the dyestuff is filtered off. This gives, after drying at about 30° to 40° C. in a vacuum cabinet, 51 g of a dark red powder.

The dyestuff has the formula ##STR14##

EXAMPLE 177

10 parts of woollen piece goods are put into a dye liquor, which contains, in 500 parts of water, 0.1 part of the dyestuff obtained in Example 176, 0.6 part of acetic acid (30% strength by weight), 0.5 part of anhydrous sodium sulphate and 0.2 part of a surface-active auxiliary, at 40° C. and the liquor is heated to 70° C. in the course of 20 minutes. The material to be dyed is moved by means of glass rods during this procedure and until the dyeing process has ended. After a residence time of 30 minutes at 70° C., the temperature of the dyebath is brought to the boiling point in the course of 30 minutes and the dyebath is kept at this temperature for 60 minutes. The dyed material is then removed from the dye liquor, rinsed with warm and then with cold water and finally dried at 60° to 70° C. This gives a clear, bluish-tinged red dyeing which is distinguished by good fastnesses to light and wet processing.

In Table 4 which follows, further reactive dyestuffs are described which are obtained by acylating the aminoazo dyestuff, used in Example 176, with the acylating agents indicated.

                  TABLE 4                                                          ______________________________________                                         Example Acylating agent       Colour shade                                     ______________________________________                                         178     Cyanuric chloride     strongly                                                                       bluish-tinged                                                                  red                                              179     Cyanuric fluoride     strongly                                                                       bluish-tinged                                                                  red                                              180     2,4-Dichloro-6-methoxy-1,3,5-                                                                        strongly                                                 triazine              bluish-tinged                                                                  red                                              181     2,4-Dichloro-6-(2-methylanilino)-                                                                    strongly                                                 1,3,5-triazine        bluish-tinged                                                                  red                                              182     2,4-Dichloro-6-anilino-1,3,5-                                                                        strongly                                                 triazine              bluish-tinged                                                                  red                                              183     2,4-Dichloro-6-(2-sulphoanilino)-                                                                    strongly                                                 1,3,5-triazine        bluish-tinged                                                                  red                                              184     2,4-Dichloro-6-(2,4-disulpho-                                                                        strongly                                                 anilino)-1,3,5-triazine                                                                              bluish-tinged                                                                  red                                              185     2,4,5,6-Tetrachloropyrimidine                                                                        strongly                                                                       bluish-tinged                                                                  red                                              186     2,4,6-Trichloropyrimidine                                                                            strongly                                                                       bluish-tinged                                                                  red                                              187     2-Methylsulphonyl-4,5-dichloro-6-                                                                    strongly                                                 methylpyrimidine      bluish-tinged                                                                  red                                              188     2,3-Dichloroquinoxaline-6-carboxylic                                                                 strongly                                                 acid chloride         bluish-tinged                                                                  red                                              189     2,3-Dichloro-quinoxaline-6-sulphonic                                                                 strongly                                                 acid chloride         bluish-tinged                                                                  red                                              190     2,4-Difluoro-6-(2,4-disulpho-                                                                        strongly                                                 anilino)-1,3,5-triazine                                                                              bluish-tinged                                                                  red                                              ______________________________________                                    

Further reactive dyestuffs, indicated in Table 5 which follows, are obtained if the aminoazo dyestuff in Example 176 is replaced by the aminoazo dyestuff of the formula ##STR15##

                  TABLE 5                                                          ______________________________________                                         Example                                                                               Acylating agent       Colour shade                                      ______________________________________                                         191    2,4,6-Trifluoro-5-chloropyrimidine                                                                   strongly bluish-                                                               tinged red                                        192    2,3-Dichloro-6-quinoxalinecarboxylic                                                                 strongly bluish-                                         acid chloride         tinged red                                        193    2,4-Dichloro-6-(2,4-disulpho-                                                                        strongly bluish-                                         anilino)-1,3,5-triazine                                                                              tinged red                                        ______________________________________                                    

EXAMPLE 194

According to the Example, a further reactive dyestuff is obtained by diazotising the amine of the formula ##STR16## and coupling the diazotisation product with 2-amino-8-hydroxynaphthalene-6-sulphonic acid, colour shade: bluish-tinged red.

EXAMPLE 195

If the diazo component in Example 194 is replaced by the amine of the formula ##STR17## A further bluish-tinged red reactive dyestuff is obtained. 

We claim:
 1. A dyestuff of the formula ##STR18## wherein R is C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy carbonyl or benzoyl.
 2. A dyestuff according to claim 1 wherein R is CH₃ CO.
 3. A dyestuff according to claim 1 wherein R is a C₁ -C₄ -alkoxycarbonyl.
 4. Azo dyestuff according to claim 1, wherein R represents C₁ -C₄ -alkylcarbonyl, benzoyl which is optionally substituted by chlorine or methyl, C₁ -C₄ -alkylaminocarbonyl or phenylaminocarbonyl which is optionally substituted by methyl or chlorine. 